Picture this: You’re excited about a new feature that could skyrocket user engagement and revenue. You share your vision with your CTO, who nods along and agrees to go for it. Fast forward three months, and what’s delivered looks nothing like what you imagined. You now think your CTO doesn’t understand the business. Sound familiar?
Here’s what happened from the CTO’s perspective. Someone had a random idea without enough detail to really judge the value. Can’t judge on the spot what that would take to implement, likely some technical complications that only show up much later. We already have a full roadmap. Let’s just nod along and deliver a minimal-impact-on-technology solution.
The CTO now thinks the CEO really doesn’t appreciate technology complexity.
There are ways to avoid this breakdown of trust, that’s what we’re on about today.
Understanding the CEO-CTO Dynamic
First things first, let’s break down what you and your CTO bring to the table:
- You, the CEO, are ultimately responsible for the company’s vision. You have the biggest picture across the company’s various parts, including the market, funding, … . Your complexity involves balancing all priorities.
- The CTO is one of those leaders with a deep understanding of the technology (and product) function and what it takes to go from idea to production. And while a good CTO also has a broad view ideally, they’re often deep first. They understand the complexity of the building.
When the roles align and work as a unit, it’s magic. But often, the magic breaks down in communicating complexity from one to the other.
Key Conversation Topics to Initiate
So, how do you get on the same page?
I’ve curated this CEO-CTO conversation starter sheet:
It is free to download, and I update it regularly.
In this article, I took out some key questions as examples and wanted to highlight the rationale behind these questions:
1. Aligning Technology Strategy for business outcomes
The “why” here should be obvious. The goal is to open a dialogue about the intersection of business and tech. Your CTO needs to understand your vision, and you need to understand the tech landscape internally and externally. Together, you can make informed decisions about trade-offs between speed, quality, and cost.
Here’s an example starter: “Our main goal is driving revenue growth. How is our tech investment stacking up towards this goal?”
2. Understanding Technical Debt and Its Business Impact
Technical debt is like financial debt but for your code. You “borrow” when you take shortcuts, make quick fixes, or just let stuff rot over time. Eventually, you’ll be in an unsustainable position. We’ve advised several clients on a recovery path, and much like in finance, it’s never easy to restructure debt once you’re too far in.
Your CTO can help you understand where you’re accruing this debt, why that is happening, and what a sensible strategy for paying down is.
Try this: “Can you explain our main areas of technical debt and how they likely impact our business right now and in the next 12 months?”
3. Realistic Timeline and Resource Planning
Unrealistic timelines are often the result of poor communication and lack of trust. Your CTO can break down the development process, helping you understand why things take the time they take and where additional resources might speed things up. And while most will argue that adding developers doesn’t produce an immediate boost in output, they certainly do so in the medium term.
Approach the conversation like this: “What’s a realistic date range for our next major update?” And then follow up with, “How could we move that date range forward?” or, alternatively, “How could we get a smaller range / more certainty on our ability to deliver in that window?”
4. Security and Compliance Considerations
Security isn’t just an IT issue; it’s a business issue. Your CTO can help you understand the security implications of your tech choices and how to strike the right balance between protection and agility.
Don’t forget this one: “Where in our organization do you see the biggest risk of cyber attacks?”
You’ll be surprised how often that isn’t your main product but targeted phishing or other weak practices outside technology. A good CTO should keep a broad view.
5. Scalability and Future-Proofing
Your tech stack needs to grow with your business. Discuss your growth projections with your CTO and understand how your current choices will support (or hinder) that growth.
Think ahead with this: “How will our current tech choices support our growth plans for the next 2-3 years?” or my favorite variation:” Where does our system break under a 10x growth scenario?” hint… it always breaks somewhere, you might just not know.
Communication Strategies for Non-Technical CEOs
Now, let’s talk about how to have these conversations effectively:
- Ask Clarifying Questions: Don’t be afraid to say, “Can you explain that in simpler terms?” or “How would that impact our users/bottom line?”
- Use Analogies: If you’re struggling to understand a concept, ask your CTO to explain it using an analogy from a field you’re familiar with.
- Regular Check-ins: Set up weekly or bi-weekly meetings precisely to align on tech strategy. This prevents small misunderstandings from becoming big problems.
Red Flags and Warning Signs
Keep an eye out for these warning signs if your tech leader or CTO shows the following:
- Reluctant to discuss timelines and drivers of uncertainty in estimates
- Not able to step away from the implementation detail and translate it outside of technical jargon
- Missed deadlines or sudden changes in project scope.
- The technology expense doesn’t seem to match the expected outcome.
- Consistently not involving yourself or other executives in strategic-level tech decisions.
If you notice these, it’s time for a frank, open discussion about communication and expectations.
Building a Collaborative Culture
Remember, great CEO-CTO relationships are built on mutual respect and trust. Encourage cross-functional teamwork, create opportunities for shared learning, and always approach tech discussions with curiosity rather than frustration.
Wrapping Up
Look, I get it. As a non-technical CEO, diving into these tech conversations can feel daunting.
But here’s what I’ve learned after years of bridging this gap: a little effort goes a long way. By initiating these conversations and showing genuine interest in understanding the tech side of your business, you’re not just improving communication – you’re setting your entire company up for success.
So, what’s your next step?
Download this CEO to CTO conversation starter sheet
Pick one of these conversation starters and schedule a chat with your CTO this week. Trust me, they’ll appreciate your interest, and you’ll gain invaluable insights into the engine that’s powering your business.
